He came up in a time when there was no money in skateboarding, and the more you stood out from the pack, the more you were loved.

Santa Cruz Skateboards legend and former recluse Jason Jessee came up in a time when there was no money in skateboarding and no rules, when the more you stood out from the pack the more you were loved. And there’s not one skater from that era who doesn’t love Jason. Every story about him is more insane and preposterous than the last, and ten times out of 11 they’re actually true. From sleeping in a room full of chickens, to being pulled off an airplane—post 9/11—for possessing a notebook with the words “suicide bomber” handwritten across it, to his sketchy motorcycle designs that have made him the toast of Tokyo, it’s safe to say googling his name will send you down a rabbithole that you won’t want to come out of for days.

The first time I met Jason was at an LA theater for a screening of Stoked, the documentary on infamous skateboarder-turned-murderer Mark ‘Gator’ Rogowski. Jason crept in a side door, unseen, and took the seat in front of me and his old friend Dave Carnie, whom he pretended not to see. He’d look away from the screen every time he appeared to deliver one of his show-stealing quotes (“Fuck limits in your life. Eat corn dogs!”), and somehow disappeared out the same door into the night without anyone realizing he’d been there. He had remained that elusive and mysterious for the past decade, until he hooked up with Converse in 2012 and slowly started to come out of his comfort zone in Watsonville, California. Now he’s traveling the world with Santa Cruz and even hosting an art show this week in Hoboken, New Jersey. I decided to call Jason to hear his version of some of his lesser-known stories and to see if I could get any intel on what exactly his “art” is (I could not).

VICE: You’re a man who wears many hats—not figuratively, but literally. How many are you wearing at the moment?Jason Jessee: Right now I have nothing to hide, but if I want, I’ll wear two because you can always take one off and then you have an extra one on. Or if someone knocks it off, you’re like, “I don’t care. I’m still wearing this one.” And if they knock that one off and you don’t have a third hat on, you’re just like, “So what? I just have to comb my hair back.” You have a few options in case you get into any street credibility issues.

What recently lit a fire under your ass? You were a recluse for many years until you got on Cons and then out of nowhere you’re all over the magazines and suddenly the skateboarding world’s darling. I was just desperate for attention. You can only sit around for so long before you’re like, My god! I’m desperate for attention. I gotta get my message to the marketplace no matter what the cost. I don’t even know what the message is but I just had to get it out there. I was bored. My friend-meter filled up and I wanted to utilize my friends. That’s exactly what happened. I’m tired of being the victim; I just want to make victims. It’s all about humor and I couldn’t laugh at my own jokes anymore. I had to get out and be a part of the world. I ran out of jokes and had to get out and do some human behavioral tests.

Got any good jokes about destroying a brand new Dodge Charger? No. Oh my god, no. That was one of my things on my dreams-come-true list—I wanted to roll a race car without getting hurt, and that’s what happened.

How fast were you going? Not fast. There just wasn’t any room for error. It went into a ditch as I was doing a boardslide with the car and then it did a 180 lipslide and then it flipped and I landed in the backseat because I never wear seatbelts and I never will. Never have and never will. It’s like you put the condom on backwards and you ended up just throwing it away. I hate putting them on because you want to exit the vehicle quick. If you get pulled over you want to be out of the vehicle before the cops, so you can be like, “Everything is OK. I’m unharmed.” So I floated into the backseat and I could hear myself telling myself, “This might not be good.” Then I landed and the windows blew out and the car landed in the ditch and the passenger door opened and I rolled out. I was standing there and I yelled, “I’m in so much trouble.” I remember yelling that. Then I remember feeling my body and going, “I’m uninjured again!” Again the human remains! That’s exactly what happened.

I’m not shitting you. And then the California Highway Patrolman was my friend and he asked what happened. I said, “I have no idea but the airbags did not deploy.” And the tow truck driver was my friend Rocky, and I was like, “What’s up, Rocky? Let me clean up for you.” So I cleaned up the mess. The next day I went skateboarding and then for one week after that day I couldn’t move and I couldn’t get out of bed. My entire body shut down. Then I had to pay my girlfriend, Jen, $4000 for her to get a new car because that was the deductible. I was like, “Fuck. Really? Four grand?” She was like, “Are you an idiot? If someone came up to you and asked if you wanted to roll a brand new race car and live with no injuries for $4000, would you?” I said, “Yeah, no problem.” And I handed her four grand and thanked her.

Is she your ex-girlfriend after that? She was already my ex-girlfriend. I lived with her but she’s my best friend. It’s like looking at your friends and knowing, I could never hump you. She’s actually like my sister. I’ll never grow up but I will mature because it’s kind of exciting and I’ve matured enough to realize my ex-girlfriend could be my best friend.

Have you matured enough that you’ve gotten rid of the metal box you used to drag behind your truck? Oh, god. That thing is gone and gone, done and done. This was a long time ago. I’m so stoked I don’t do anything like that anymore. It was a metal box that was chained on the back of my truck and I could knock it off. You could do that and people would be like, “Holy shit!” They would clear out of the way. I took it on the freeway before and you would see people getting over and parking in the emergency lane. It was really fun. I had a little rope and I’d yank it and the metal box would drop off the truck and the chain was like 40 feet long and people would back the fuck off. It was the best shit ever. It was maybe my favorite time of life because it was just sketchy. And cops would just wave to me. I’d run red lights in front of cops and they’d just be like, “Hey, what’s up, Jason?” I swear to god. They didn’t like me but they just didn’t care. I talk to cops about it now and they tell me, “We used to drive by your warehouse and see the shit you were doing and just crack up.”

If you had a chance to get your hands on it, would you have done that chain trick with Steve Claar’s leg? Oh my god! I called Steve Claar and the first thing I said was, “Can I keep your amputated leg? Please say I can have your leg.” And he was like, “I already asked because I knew you were going to ask me and they already threw it away. They have to dispose of it. They told me it was illegal for me to take it home.” Man, how rad would it be to beat your neighbor with your leg? I love Steve Claar. Do you have any idea how many frontside ollies that leg has done?

Do you think if you strapped his amputated leg to your leg you’d go extra high? No, but you’d have a limp that wouldn’t go away, for sure. And your friends would be like, “Do you think that limp will go away?” Steve has a limp. It’s kind of weird. It won’t go away. I asked him. That’s why I don’t talk to him anymore. Would you want to cruise around with your friend with a limp? And you have that pressure to tell people he has a fake leg and that he had it removed, not from Vietnam but from smoking. It’s like you want to put them down. You see dogs that limp and you want to put it down. It’s natural human instinct that the strong shall survive and yet the weak are still here. It’s like a Devo quote.

Speaking of Devo, how did you come up on a Devo guitar? From John Schuller. I traded a bicycle for it like 20 years ago. I kept it in good condition and then Bob [Casale] found out that I had it and I gave it back to him. It was the Devo cloud guitar and he said it was his favorite guitar and it plays exactly the same as it did. He said he went through a weird month where he had to give everything to a pawn shop and he went back to get it but it was gone because it got stolen. And I was like, “I didn’t steal it!” He didn’t think I did.

How is it that you’re big in Japan? I’m not. I’m not even 6’4”. I’ve never even been to Japan. I have no idea. It’s because Japanese people come and visit me and I’m so nice to them and ask them if they want to do this or this or this and then they go back and tell their friends, “We went to Jason’s house and had so much fun!” You know how rumors start in Japan; it’s crazy over there. I tell them stuff, like I have Steve Claar’s foot and I show them real fast and it’s a big, fake Halloween foot and they’re like, “Oh my god! He does!” Then they go back and tell their friends that I have stool samples of my friends. But I’ve never been there. I’m never going. It’s so far away. Do you know how much a first-class ticket would be to Japan? Like ten grand. There’s no sponsors that would pay that.

You’re only flying first class? Is that your deal now? Well, yeah—if you want to take me to Japan. There’s no way I’m going to sit coach or in the back where everyone smokes. I want to sit first class.

I know you always built motorcycles and that’s what they love you for in Japan. But you have an art show this Thursday in Hoboken. Is that a new thing? Are you the next great skate artist? No, I’m not an artist. I don’t even draw. I just screen boards and then I destroy them with paint pens. It’s just a front for a meet and greet. I just want to meet new friends so I pretend I’m an artist and have art shows. Then when people show, I’m like, “Can I get your number? Your Instagram? If I’m ever in New Jersey I’m gonna hit you up so we can eat sandwiches and snacks.” That’s all it is. It’s just a ruse to get in and see who everyone is.

What should people expect from the show? I’m not bringing anything to the table. I just want everyone to be themselves. I don’t want anyone to act weird or act out. I might not even show up. I don’t have anything prepared. I’m probably going to stop at a skateshop somewhere and buy some boards and hang up someone else’s boards and be like, “This is my work and this is what I envisioned.”

On a final note, we lost Jay Adams recently—rest in peace. I refuse to believe that he is gone. But go on.

Every time you ran into Jay he was just the best and made it so memorable. I remember I first met him at a trade show and he was like, “Nieratko! You gotta meet my chick!” And he just took my hand and shoved it up his girl’s skirt and tried to jam it up inside her. It was insane. I know you guys were close. What’s your best Jay Adams story? There’s too many to tell just one. He was the best dude ever. Everyone has such good Jay stories. People thought they had Duane [Peters] stories? Oh man. Anyone who ever interacted with Jay in any way had the raddest experience. He’s the epic human being in skateboarding. Someone asked me to write something about Jay but keep it G-Rated. I was like, “Nope, I’m out. Absolutely not.” But I will tell you, when I was 17, I learned common courtesy and consideration from him. We paddled out at Oxnard and there were all these sketchy locals out there. I was like, “Jay, we shouldn’t surf here. It’s sketchy. Those guys over there are sketchy.” And he was like, “What? Fuck that! I want to go meet them.” And he goes and paddles out and goes right up to them all crazy and says, “What’s up? I’m Jay Adams.” Not Jay Adams the skateboarder, just Jay Adams the human being. He shook all their hands, introduced me and then asked, “Is it cool if we surf out here?” They were like, “Oh, hell yeah. No problem.” It wasn’t like they knew him as Jay Adams; he was just cool. And they were a little bit nervous about him because they were kinda sketchy and he was sketchy and came right up to all of them.

He told me afterwards, “You just have to be cool and be considerate.” When I first met him I was, like, 12. And we all know the impact that he had on every human being’s life that he met. He rules. He was terrifying but the nicest, terrifying human ever.

OK, I gotta go. I’ll see you in New Jersey. Hey, when I get there I want to go to the Jersey Shore to tan. And I want to go to the gym and I want to do my laundry. I want to lay my towel out and I want somebody to walk by and kick sand on me and then I could be like, “We’re fucking out of here!” And then we go to the gym.

Sounds like a situation.

Follow Jason Jessee on Instagram and come out to NJ Skateshop in Hoboken, NJ on Thursday, September 25 to meet him in person at the art show.